# RENKIN building blocks — commercially available starting materials
# Format: SMILES  name (whitespace-delimited)
# ~400 entries covering aliphatics, carbonyls, acids, alcohols, amines,
# halides, boronic acids, heterocycles, amino acids, sulfonyl chlorides,
# acyl chlorides, and protecting-group precursors.

# ── Simple aliphatics ─────────────────────────────────────────────────────────
C               methane
CC              ethane
CCC             propane
CCCC            butane
CCCCC           pentane
C(=O)O          formic_acid
CC(=O)O         acetic_acid
CCC(=O)O        propionic_acid
CCCC(=O)O       butyric_acid
CC(C)C(=O)O     isobutyric_acid
O               water
N               ammonia
CCO             ethanol
CO              methanol
CCCO            1-propanol
CC(O)C          isopropanol
CCCCO           1-butanol
CC(O)CC         2-butanol
OC(C)(C)C       tert-butanol
ClCCl           dichloromethane
ClCl            chlorine
CBr             methyl_bromide
CCBr            ethyl_bromide
CCCBr           1-bromopropane
CCCl            1-chloropropane
CCCCBr          1-bromobutane
BrCCBr          1-2-dibromoethane

# ── Acyl chlorides ────────────────────────────────────────────────────────────
CC(=O)Cl        acetyl_chloride
CCC(=O)Cl       propanoyl_chloride
CCCC(=O)Cl      butanoyl_chloride
ClC(=O)CCl      malonyl_dichloride
ClC(=O)c1ccccc1 benzoyl_chloride
ClC(=O)c1ccc(N)cc1  4-aminobenzoyl_chloride
ClC(=O)c1ccc(Cl)cc1 4-chlorobenzoyl_chloride
ClC(=O)c1ccc(OC)cc1 4-methoxybenzoyl_chloride
ClC(=O)c1ccncc1 isonicotinoyl_chloride
ClC(=O)CCCl     3-chloropropanoyl_chloride

# ── Carbonyls (aldehydes / ketones) — for reductive amination / Wittig ───────
O=C             formaldehyde
CC=O            acetaldehyde
CCC=O           propanal
CCCC=O          butanal
CC(=O)C         acetone
CC(=O)CC        methyl_ethyl_ketone
CC(=O)CCC       methyl_propyl_ketone
O=Cc1ccccc1     benzaldehyde
O=Cc1ccc(O)cc1  4-hydroxybenzaldehyde
O=Cc1ccc(N)cc1  4-aminobenzaldehyde
O=Cc1cccnc1     nicotinaldehyde
O=Cc1ccncc1     isonicotinaldehyde
O=Cc1ccc(OC)cc1 4-methoxybenzaldehyde
O=Cc1ccc(Cl)cc1 4-chlorobenzaldehyde
O=Cc1ccc(F)cc1  4-fluorobenzaldehyde
O=Cc1ccc(Br)cc1 4-bromobenzaldehyde
O=C(C)c1ccccc1  acetophenone
O=C(C)c1ccc(N)cc1  4-aminoacetophenone
O=C(C)c1ccc(O)cc1  4-hydroxyacetophenone
O=C(C)c1ccc(Cl)cc1 4-chloroacetophenone
O=C(C)c1ccc(OC)cc1 4-methoxyacetophenone
CC(=O)CC(=O)C   acetylacetone
O=C1CCCC1       cyclopentanone
O=C1CCCCC1      cyclohexanone

# ── Carboxylic acids ──────────────────────────────────────────────────────────
OC(=O)CC(=O)O   malonic_acid
OC(=O)CCC(=O)O  succinic_acid
OC(=O)CCCC(=O)O glutaric_acid
OC(=O)CCCCC(=O)O adipic_acid
OC(=O)c1ccccc1  benzoic_acid
OC(=O)c1ccc(N)cc1  4-aminobenzoic_acid_PABA
OC(=O)c1ccc(O)cc1  4-hydroxybenzoic_acid
OC(=O)c1ccc(Cl)cc1 4-chlorobenzoic_acid
OC(=O)c1ccc(F)cc1  4-fluorobenzoic_acid
OC(=O)c1ccc(OC)cc1 4-methoxybenzoic_acid
OC(=O)c1ccc(C)cc1  4-methylbenzoic_acid
OC(=O)c1ccc(Br)cc1 4-bromobenzoic_acid
OC(=O)c1ccncc1  isonicotinic_acid
OC(=O)c1cccnc1  nicotinic_acid
OC(=O)c1ccccn1  picolinic_acid
OC(=O)c1ccc(N)cc1N  anthranilic_acid_equiv
CC(O)C(=O)O     lactic_acid
OCC(=O)O        glycolic_acid
OC(=O)c1ccccc1C(=O)O phthalic_acid
OC(=O)c1cccc(C(=O)O)c1 isophthalic_acid
OC(=O)c1ccc(C(=O)O)cc1 terephthalic_acid
OC(=O)/C=C/C(=O)O fumaric_acid
OC(=O)CCNC(=O)O Boc-GABA-like

# ── Alcohols / phenols ────────────────────────────────────────────────────────
Oc1ccccc1       phenol
Oc1ccc(O)cc1    hydroquinone
Oc1ccccc1C(=O)O salicylic_acid
Oc1ccc(N)cc1    4-aminophenol
Oc1ccncc1       4-hydroxypyridine
Oc1ccc(Cl)cc1   4-chlorophenol
Oc1ccc(F)cc1    4-fluorophenol
Oc1ccc(Br)cc1   4-bromophenol
Oc1ccc(OC)cc1   4-methoxyphenol
Oc1ccc(C)cc1    4-methylphenol_cresol
Oc1cccc(O)c1    resorcinol
Oc1ccc(C(=O)O)cc1  4-hydroxybenzoic_acid_alt
OCC             ethylene_glycol
OCCO            ethylene_glycol_alt
OC(CO)CO        glycerol
OCCc1ccccc1     2-phenylethanol
OCc1ccccc1      benzyl_alcohol
OCc1ccc(O)cc1   4-hydroxybenzyl_alcohol
OCc1ccc(N)cc1   4-aminobenzyl_alcohol

# ── Primary amines ────────────────────────────────────────────────────────────
CN              methylamine
CCN             ethylamine
CCCN            propylamine
CCCCN           n-butylamine
CC(N)C          isopropylamine
CC(C)(C)N       tert-butylamine
NCC(=O)O        glycine
NCc1ccccc1      benzylamine
Nc1ccccc1       aniline
Nc1ccc(N)cc1    p-phenylenediamine
Nc1cccc(N)c1    m-phenylenediamine
Nc1ccc(F)cc1    4-fluoroaniline
Nc1ccc(Cl)cc1   4-chloroaniline
Nc1ccc(Br)cc1   4-bromoaniline
Nc1ccc(OC)cc1   4-methoxyaniline
Nc1ccc(C)cc1    4-methylaniline
Nc1ccc(C(=O)O)cc1 4-aminobenzoic_acid_amine_form
Nc1ccncc1       4-aminopyridine
Nc1cccnc1       3-aminopyridine
Nc1ccccn1       2-aminopyridine
c1ccc(N)cc1C(=O)O  anthranilic_acid
c1cc(N)ccc1C(=O)O  3-aminobenzoic_acid
NCC             ethylamine_alt
NCCc1ccccc1     2-phenylethylamine
NCc1ccc(O)cc1   tyramine
NCc1ccncc1      4-pyridylmethylamine
NCCN            1-2-diaminoethane
NCCCN           1-3-diaminopropane
NC1CCCC1        cyclopentylamine
NC1CCCCC1       cyclohexylamine

# ── Secondary / cyclic amines ─────────────────────────────────────────────────
C1CCNCC1        piperidine
C1CCOC1         tetrahydrofuran
C1CNCCN1        piperazine
N1CCOCC1        morpholine
C1CCNC1         pyrrolidine
C1CCCCN1        azepane
C1CCN(CC1)C     N-methylpiperidine
C1CCN(CC1)CC    N-ethylpiperidine
C1CN(CCN1)C     N-methylpiperazine
CNCCN(C)C       not_valid_placeholder
c1cc[nH]c1      pyrrole_NH
c1cnc[nH]1      imidazole_NH
c1cn[nH]c1      pyrazole_NH
C1CC1N          cyclopropylamine
C1CCC1N         cyclobutylamine
OCCN            ethanolamine
OCCNCC          N-ethylethanolamine
CN(C)CCO        DMAE

# ── Aromatic halides (for Suzuki / Buchwald coupling) ────────────────────────
Brc1ccccc1      bromobenzene
Brc1ccc(N)cc1   4-bromoaniline
Brc1ccc(O)cc1   4-bromophenol
Brc1ccc(OC)cc1  4-bromoanisole
Brc1ccc(C)cc1   4-bromotoluene
Brc1ccc(F)cc1   4-fluorobromobenzene
Brc1ccc(Cl)cc1  4-chlorobromobenzene
Brc1cccc(Br)c1  1-3-dibromobenzene
Brc1ccc(C(=O)O)cc1  4-bromobenzoic_acid
Brc1ccc(C=O)cc1 4-bromobenzaldehyde_br
Brc1ccc(C(=O)C)cc1  4-bromoacetophenone
Clc1ccccc1      chlorobenzene
Clc1ccc(N)cc1   4-chloroaniline
Clc1ccc(OC)cc1  4-chloroanisole
Clc1ccc(C(=O)O)cc1  4-chlorobenzoic_acid
Fc1ccccc1       fluorobenzene
Fc1ccc(N)cc1    4-fluoroaniline
Fc1ccc(OC)cc1   4-fluoroanisole
Ic1ccccc1       iodobenzene
Ic1ccc(N)cc1    4-iodoaniline
Ic1ccc(OC)cc1   4-iodoanisole
Brc1ccncc1      4-bromopyridine
Brc1cccnc1      3-bromopyridine
Brc1ccccn1      2-bromopyridine
Clc1ccncc1      4-chloropyridine
Clc1cccnc1      3-chloropyridine
Clc1ccccn1      2-chloropyridine
Brc1ccc2ccccc2c1  2-bromonaphthalene
Brc1ccc2ncccc2c1  2-bromoquinoline_like

# ── Boronic acids (for Suzuki coupling) ──────────────────────────────────────
OB(O)c1ccccc1   phenylboronic_acid
OB(O)c1ccc(F)cc1   4-fluorophenylboronic_acid
OB(O)c1ccc(Cl)cc1  4-chlorophenylboronic_acid
OB(O)c1ccc(Br)cc1  4-bromophenylboronic_acid
OB(O)c1ccc(OC)cc1  4-methoxyphenylboronic_acid
OB(O)c1ccc(N)cc1   4-aminophenylboronic_acid
OB(O)c1ccc(C)cc1   4-methylphenylboronic_acid
OB(O)c1ccc(C(=O)O)cc1 4-carboxyphenylboronic_acid
OB(O)c1ccncc1   4-pyridylboronic_acid
OB(O)c1cccnc1   3-pyridylboronic_acid
OB(O)c1ccccn1   2-pyridylboronic_acid
OB(O)c1ccc2ccccc2c1 2-naphthylboronic_acid

# ── Heterocycles ──────────────────────────────────────────────────────────────
c1ccccc1        benzene
c1ccncc1        pyridine
c1ccco1         furan
c1cccs1         thiophene
c1cnco1         oxazole
c1csc[nH]1      thiazole
c1ccno1         isoxazole
c1ccnc(N)c1     2-aminopyrimidine
c1ccncc1N       3-aminopyridine_het
c1ccc2[nH]ccc2c1  indole
c1ccc2[nH]nnc2c1  indazole
c1cnc2ccccc2n1  benzimidazole
c1csc2ccccc12   benzothiazole
c1coc2ccccc12   benzofuran
c1ccc2ncccc2c1  quinoline
c1ccnc2ccccc12  isoquinoline
c1cnc2ccccc2c1  quinazoline_like
C1CCCO1         tetrahydrofuran_alt
C1CCCCO1        tetrahydropyran
c1ccnc(Cl)c1    2-chloropyridine_het
c1ccncc1Cl      3-chloropyridine_het
c1ccc(cc1)N     aniline_alt

# ── Amino acids (common, free form) ──────────────────────────────────────────
NC(C)C(=O)O         alanine_Ala
NC(CC(=O)O)C(=O)O   aspartic_acid_Asp
NC(CCC(=O)O)C(=O)O  glutamic_acid_Glu
NC(CO)C(=O)O        serine_Ser
NC(Cc1ccccc1)C(=O)O phenylalanine_Phe
NC(Cc1ccc(O)cc1)C(=O)O tyrosine_Tyr
NC(CCCCN)C(=O)O     lysine_Lys
NC(CS)C(=O)O        cysteine_Cys
NC(C(C)C)C(=O)O     valine_Val

# ── Sulfonyl chlorides ────────────────────────────────────────────────────────
CS(=O)(=O)Cl        methanesulfonyl_chloride_MsCl
CCS(=O)(=O)Cl       ethanesulfonyl_chloride
c1ccc(S(=O)(=O)Cl)cc1  benzenesulfonyl_chloride
Cc1ccc(S(=O)(=O)Cl)cc1  tosyl_chloride_TsCl
Fc1ccc(S(=O)(=O)Cl)cc1  4-fluorobenzenesulfonyl_chloride
Nc1ccc(S(=O)(=O)Cl)cc1  4-aminobenzenesulfonyl_chloride

# ── Isocyanates / carbamates (for urea / carbamate retro) ────────────────────
CN=C=O          methyl_isocyanate
CCN=C=O         ethyl_isocyanate
c1ccccc1N=C=O   phenyl_isocyanate
O=C(OCC)OCC     diethyl_carbonate
CC(=O)OC(C)(C)C Boc_tBuOAc_equiv

# ── Protecting group precursors ───────────────────────────────────────────────
ClC(=O)OCC1=CC=CC=C1  Cbz-Cl
OC(=O)OC(C)(C)C     Boc-OH
CC(C)(C)OC(=O)Cl    Boc-Cl
CC1(C)OCC(CO1)      neopentyl_glycol_like

# ── Aryl / heteroaryl bromides (Suzuki / Buchwald / Negishi donors) ───────────
Brc1ccc(C#N)cc1     4-bromobenzonitrile
Brc1ccc(CC)cc1      4-bromoethylbenzene
Brc1cc(OC)ccc1OC    2-bromo-4-5-dimethoxybenzene
Brc1ccc(N+](=O)[O-])cc1  4-bromonitrobenzene
Brc1ccc(Br)cc1      1-4-dibromobenzene
Brc1ccccc1Br        1-2-dibromobenzene
Brc1cncc1           3-bromo-4-azapyridine
Brc1ccncc1OC        4-bromo-3-methoxypyridine
Brc1ccc2[nH]ccc2c1  5-bromoindole
Brc1cccc2ccccc12    1-bromonaphthalene
Brc1ccc2cccc(c2n1)  3-bromoisoquinoline
Brc1cnc2ccccc2n1    2-bromobenzimidazole
Brc1sc2ccccc2n1     2-bromobenzothiazole
Brc1oc2ccccc2n1     2-bromobenzoxazole
Brc1cnc(N)nc1       2-amino-5-bromopyrimidine
Brc1ccc(Br)nc1      2-5-dibromopyridine
Brc1ccnc(N)c1       5-bromo-2-aminopyridine
Brc1ccc(F)cn1       5-bromo-2-fluoropyridine
Brc1cccc(C=O)c1     3-bromobenzaldehyde
Brc1ccc(cc1)C(=O)C  4-bromoacetophenone
Brc1ccc(C(F)(F)F)cc1 4-bromo-trifluoromethylbenzene
Brc1ccc2ccncc2c1    6-bromoisoquinoline
Brc1cncc2ccccc12    3-bromoquinoxaline

# ── Aryl chlorides (SNAr, Pd-C-Cl activation donors) ────────────────────────
Clc1ccc(Cl)cc1      1-4-dichlorobenzene
Clc1ccc(F)cc1       4-chlorofluorobenzene
Clc1ccc(C#N)cc1     4-chlorobenzonitrile
Clc1cnc(Cl)nc1      2-4-dichloropyrimidine
Clc1ccnc(Cl)c1      2-5-dichloropyridine
Clc1nccc2ccccc12    4-chloroquinoline
Clc1cnc2ccccc2n1    2-chlorobenzimidazole
Clc1cccc2ncccc12    4-chloroisoquinoline
Clc1ccc(N+](=O)[O-])cc1 4-chloronitrobenzene
Clc1ccc(CF)cc1      4-chloro-benzyl_fluoride
Clc1nc(Cl)nc(Cl)n1  2-4-6-trichlorotriazine

# ── Boronic acids / pinacol boronates (Suzuki acceptors) ─────────────────────
OB(O)c1ccc(C#N)cc1      4-cyanophenylboronic_acid
OB(O)c1ccc(C(F)(F)F)cc1 4-trifluoromethylphenylboronic_acid
OB(O)c1ccc2[nH]ccc2c1   5-indoleboronic_acid
OB(O)c1ccc2ncccc2c1     3-quinolineboronic_acid
OB(O)c1ccc(N+](=O)[O-])cc1 4-nitrophenylboronic_acid
OB(O)c1cccc(OC)c1       3-methoxyphenylboronic_acid
OB(O)c1ccc(CC)cc1       4-ethylphenylboronic_acid
B1(OC(C)(C)C(C)(C)O1)c1ccccc1  phenylboronic_pinacol_ester

# ── Pyridines (methyl/halo/amino substituted) ────────────────────────────────
Cc1ccccn1           2-methylpyridine
Cc1cccnc1           3-methylpyridine
Cc1ccncc1           4-methylpyridine
Cc1cccc(C)n1        2-6-dimethylpyridine
Cc1ccc(C)cn1        2-4-dimethylpyridine
Nc1cccc(N)n1        2-6-diaminopyridine
OC1=CC=CC=N1        2-hydroxypyridine
OC1=NC=CC=C1        3-hydroxypyridine
FC1=CC=CN=C1        2-fluoropyridine
FC1=CC=NC=C1        3-fluoropyridine
FC1=CC=CC=N1        2-6-difluoropyridine
c1cc2ccccc2nc1      quinoline_alt
Cc1ccncc1C          3-5-dimethylpyridine
Cc1nc(C)cc(C)c1     2-4-6-trimethylpyridine

# ── Pyrimidines and diazines ──────────────────────────────────────────────────
c1ccnc(N)c1N        2-3-diaminopyridine
Nc1ncccn1           2-aminopyrimidine_alt
Nc1nccnc1           2-aminopyrazine
Nc1ncncc1           2-aminopyrimidine
c1cnc(N)nc1         2-aminopyrimidine_4
Cc1ncccn1           2-methylpyrimidine
Cc1ccnc(N)c1        2-amino-4-methylpyridine
c1ccnc(Cl)n1        2-chloropyrimidine
c1ccnc(N)n1         2-aminopyrimidine
Clc1ccnc(Cl)n1      2-4-dichloropyrimidine

# ── Pyrazoles and imidazoles (37% of unsolved!) ──────────────────────────────
c1c[nH]nc1              imidazole_alt
Cc1cc[nH]n1             3-methylpyrazole
Cc1ccn[nH]1             5-methylpyrazole
Cc1cc(C)n[nH]1          3-5-dimethylpyrazole
c1c[nH]nn1              1H-tetrazole
c1cc[nH]n1              1H-pyrazole
c1c[nH]cn1              imidazole
Cn1ccnc1                1-methylimidazole
Cc1cnc[nH]1             4-methylimidazole
Cc1ncc[nH]1             2-methylimidazole
c1cncs1                 thiazole
Cc1csc[nH]1             4-methylthiazole
c1ncs[nH]1              thiadiazole
c1nnco1                 1-2-4-oxadiazole
c1nncs1                 1-2-4-thiadiazole
Cc1ccc[nH]1             3-methylpyrrole
c1cco[nH]1              isoxazole_like
Cn1cccc1                1-methylpyrrole
Cn1cncn1                1-methyltetrazole
Cn1ccc(C)c1C            1-2-4-trimethylpyrrole

# ── Furans and thiophenes ─────────────────────────────────────────────────────
c1ccoc1                 furan
c1ccsc1                 thiophene
Cc1ccco1                2-methylfuran
Cc1cccs1                2-methylthiophene
Brc1ccco1               2-bromofuran
Brc1cccs1               2-bromothiophene
Brc1ccc(s1)C            5-bromo-2-methylthiophene
c1cc2ccccc2o1           benzofuran_alt
c1cc2ccccc2s1           benzothiophene
Brc1cc2ccccc2o1         3-bromobenzofuran
OB(O)c1ccco1            furan-2-boronic_acid
OB(O)c1cccs1            thiophen-2-boronic_acid

# ── Common pharma amines and protected amines ────────────────────────────────
C1COCCN1                morpholine
C1CCN(CC1)C(=O)OC(C)(C)C   N-Boc-piperidine
C1CN(CCO1)C(=O)OC(C)(C)C   N-Boc-morpholine
C1CN(CCN1)C(=O)OC(C)(C)C   N-Boc-piperazine
C(C(=O)O)(N)CCC         homoserine_like
CCN(CC)CC               triethylamine
CN(C)C                  trimethylamine
CNC                     dimethylamine
C(C)(C)N                tert-butylamine
CCN(C)C                 dimethylethylamine
C(CC)N                  propylamine
NCC1CCCC1               cyclopentylmethylamine
NCC1CCCCC1              cyclohexylmethylamine
N1CCNCC1                piperazine_alt
C1CCCC1N                cyclopentylamine_alt
c1ccc(cc1)CN            benzylamine
c1ccc(cc1)N(C)C         N-N-dimethylaniline
c1cccc(N)c1             3-aminobenzene
c1ccc(N)c(N)c1          1-2-phenylenediamine

# ── Aldehydes (for reductive amination / condensation) ───────────────────────
O=Cc1ccccn1             2-pyridinecarboxaldehyde
O=Cc1ccc(C(F)(F)F)cc1   4-trifluoromethylbenzaldehyde
O=Cc1ccc(C#N)cc1        4-cyanobenzaldehyde
O=Cc1ccco1              furfural
O=Cc1cccs1              thiophene-2-carboxaldehyde
O=CC1CCCC1              cyclopentanecarbaldehyde
O=CC1CCCCC1             cyclohexanecarbaldehyde
CC(=O)c1ccccc1          acetophenone
CC(=O)c1ccccn1          2-acetylpyridine
CC(=O)c1cccnc1          3-acetylpyridine
CC(=O)c1ccncc1          4-acetylpyridine

# ── Common acids for amide coupling ──────────────────────────────────────────
OC(=O)c1ccco1           2-furoic_acid
OC(=O)c1cccs1           2-thenoic_acid
OC(=O)c1ccc2[nH]ccc2c1  indole-5-carboxylic_acid
OC(=O)c1ccc(C(F)(F)F)cc1 4-trifluoromethylbenzoic_acid
OC(=O)c1ccc(C#N)cc1     4-cyanobenzoic_acid
OC(=O)c1cc(Cl)ccc1Cl    2-4-dichlorobenzoic_acid
OC(=O)CC1CCCC1          cyclopentylacetic_acid
OC(=O)CC1CCCCC1         cyclohexylacetic_acid
OC(=O)Cc1ccccc1         phenylacetic_acid
OC(=O)Cc1ccccn1         2-pyridylacetic_acid

# ── Nitrile precursors ────────────────────────────────────────────────────────
N#Cc1ccccc1             benzonitrile
N#Cc1ccccn1             2-pyridinecarbonitrile
N#Cc1cccnc1             3-pyridinecarbonitrile
N#Cc1ccncc1             4-pyridinecarbonitrile
N#Cc1ccc(F)cc1          4-fluorobenzonitrile
N#Cc1ccc(Cl)cc1         4-chlorobenzonitrile
N#Cc1ccc(OC)cc1         4-methoxybenzonitrile
N#CC1CCCC1              cyclopentanecarbonitrile
N#CC1CCCCC1             cyclohexanecarbonitrile
N#CCC(=O)c1ccccc1       benzoylacetonitrile

# ── Halogenated aromatics (for Grignard / Li-halogen exchange) ───────────────
Ic1ccccn1               2-iodopyridine
Ic1cccnc1               3-iodopyridine
Ic1ccncc1               4-iodopyridine
Ic1ccc(F)cc1            4-fluoroiodobenzene
Fc1ccc(F)cc1            4-4-difluorobenzene
Fc1ccccc1F              1-2-difluorobenzene
Fc1cccc(F)c1            1-3-difluorobenzene
Fc1ccccn1               2-fluoropyridine
FC(F)(F)c1ccccc1        trifluoromethylbenzene
FC(F)(F)c1ccccn1        2-trifluoromethylpyridine
FC(F)(F)c1cccnc1        3-trifluoromethylpyridine
FC(F)(F)c1ccncc1        4-trifluoromethylpyridine
FC(F)(F)c1cccc(F)c1     3-fluorobenzotrifluoride
OC(F)(F)F               trifluoromethanol
COC(F)(F)F              methyl_trifluoromethyl_ether
OC(F)F                  difluoromethanol
# ── Trifluoromethoxy (OCF3) arenes ──────────────────────────────────────────
FC(F)(F)Oc1ccccc1        trifluoromethoxybenzene
FC(F)(F)Oc1ccc(Br)cc1   4-bromo-trifluoromethoxybenzene
FC(F)(F)Oc1ccc(Cl)cc1   4-chloro-trifluoromethoxybenzene
FC(F)(F)Oc1ccc(N)cc1    4-amino-trifluoromethoxybenzene
OB(O)c1ccc(OC(F)(F)F)cc1   4-trifluoromethoxyphenylboronic_acid
FC(F)(F)Oc1ccc(F)cc1    4-fluoro-trifluoromethoxybenzene
FC(F)(F)Oc1cccc(Br)c1   3-bromo-trifluoromethoxybenzene
FC(F)(F)Oc1ccccn1        2-trifluoromethoxypyridine
FC(F)(F)Oc1cccnc1        3-trifluoromethoxypyridine
FC(F)(F)Oc1ccncc1        4-trifluoromethoxypyridine
# ── ArCF3 amines / halides (missing isomers) ─────────────────────────────────
Nc1ccc(C(F)(F)F)cc1     4-aminobenzotrifluoride
Nc1cccc(C(F)(F)F)c1     3-aminobenzotrifluoride
Nc1ccccc1C(F)(F)F       2-aminobenzotrifluoride
Clc1ccc(C(F)(F)F)cc1    4-chlorobenzotrifluoride
Clc1cccc(C(F)(F)F)c1    3-chlorobenzotrifluoride
Brc1cccc(C(F)(F)F)c1    3-bromotrifluoromethylbenzene
OB(O)c1cccc(C(F)(F)F)c1 3-trifluoromethylphenylboronic_acid
OB(O)c1cc(C(F)(F)F)ccc1 2-trifluoromethylphenylboronic_acid
# ── CF3CH2 (2,2,2-trifluoroethyl) ───────────────────────────────────────────
OCC(F)(F)F              2,2,2-trifluoroethanol
NCC(F)(F)F              2,2,2-trifluoroethylamine
BrCC(F)(F)F             2,2,2-trifluoroethyl_bromide
# ── Nitrile BBs (aryl nitriles for Sandmeyer / C-N disconnections) ──
N#Cc1ccc(Br)cc1         4-bromobenzonitrile
N#Cc1ccc([NH2])cc1      4-aminobenzonitrile
# ── Sulfonyl chlorides (for sulfonamide_retro + diaryl_sulfone_retro) ────────
CS(=O)(=O)O             methanesulfonic_acid
CCCS(=O)(=O)Cl          propane-1-sulfonyl_chloride
CC(C)S(=O)(=O)Cl        isopropylsulfonyl_chloride
O=S(=O)(Cl)c1ccccc1     benzenesulfonyl_chloride
Clc1ccc(S(=O)(=O)Cl)cc1 4-chlorobenzenesulfonyl_chloride
O=S(=O)(Cl)c1cccc(F)c1  3-fluorobenzenesulfonyl_chloride
Cc1ccc(S(=O)(=O)Cl)nc1  5-methylpyridine-2-sulfonyl_chloride
O=S(=O)(Cl)c1ccc(OC)cc1 4-methoxybenzenesulfonyl_chloride
# heteroaryl sulfonyl chlorides (key for drug sulfonamides)
O=S(=O)(Cl)c1ccccn1     pyridine-2-sulfonyl_chloride
O=S(=O)(Cl)c1cccnc1     pyridine-3-sulfonyl_chloride
O=S(=O)(Cl)c1ccncc1     pyridine-4-sulfonyl_chloride
O=S(=O)(Cl)c1ncccn1     pyrimidine-2-sulfonyl_chloride
O=S(=O)(Cl)c1csc(=N)n1  2-aminothiazole-5-sulfonyl_chloride
O=S(=O)(Cl)c1cccs1      thiophene-2-sulfonyl_chloride
O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1  4-(trifluoromethyl)benzenesulfonyl_chloride
O=S(=O)(Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1  3,5-bis(trifluoromethyl)benzenesulfonyl_chloride
FC(F)(F)S(=O)(=O)Cl     trifluoromethanesulfonyl_chloride
O=S(=O)(Cl)c1ccc2ccccc2c1  2-naphthalenesulfonyl_chloride
O=S(=O)(Cl)c1ccnc2ccccc12  quinoline-8-sulfonyl_chloride
# common sulfonamide synthons (appear as BB in fragment-based synthesis)
NS(=O)(=O)c1ccccc1      benzenesulfonamide
NS(=O)(=O)c1ccc(Cl)cc1  4-chlorobenzenesulfonamide
NS(=O)(=O)C             methanesulfonamide
# ── Activated alkyl BBs ──
BrCc1ccccn1             2-pyridylmethyl_bromide
BrCc1cccnc1             3-pyridylmethyl_bromide
