trans-2-Phenylcyclopropanecarbonyl chloride

Base Information

• Chemical Name: trans-2-Phenylcyclopropanecarbonyl chloride
• CAS No.: 939-87-7
• Molecular Formula: C₁₀H₉ClO
• Molecular Weight: 180.634
• Hs Code.: 2916399090
• European Community (EC) Number: 213-365-8
• NSC Number: 80667
• DSSTox Substance ID: DTXSID001246007
• Nikkaji Number: J232.202A
• Wikidata: Q76000552
• Mol file: 939-87-7.mol

Synonyms:939-87-7;trans-2-Phenylcyclopropanecarbonyl chloride;trans-2-Phenyl-1-cyclopropanecarbonyl chloride;(1R,2R)-2-phenylcyclopropane-1-carbonyl chloride;EINECS 213-365-8;trans-2-Phenylcyclopropane-1-carboxylic acid chloride;(1R,2R)-2-phenylcyclopropanecarbonyl chloride;NSC 80667;CYCLOPROPANECARBONYL CHLORIDE, 2-PHENYL-, (E)-;37107-48-5;Cyclopropanecarbonyl chloride, 2-phenyl-, (1R,2R)-rel-;Cyclopropanecarbonyl chloride, 2-phenyl-, trans-;2-Phenylcyclopropanecarbonyl chloride #;2-Phenylcyclopropanecarbonyl chloride, trans-;SCHEMBL452300;WLN: L3TJ AVG BR -E;DTXSID001246007;NSC80667;Cyclopropanecarbonyl chloride, (E)-;Cyclopropanecarbonyl chloride, trans-;MFCD00001278;NSC-80667;AKOS015913491;LS-58523;trans-2-phenylcyclopropylcarbonyl chloride;trans-2-phenyl-cyclopropanecarbonyl chloride;trans-2-phenyl-cyclopropane carbonyl chloride;(1R,2R)-2-phenylcyclopropanecarbonylchloride;trans-2-phenyl-1-cyclopropylcarbonyl chloride;trans-2-phenylcyclopropane-1-carbonyl chloride;trans-2-phenyl cyclopropan-1-carbonyl chloride;2alpha-Phenyl-1beta-cyclopropanecarbonyl chloride;(+/-)-trans-2-phenylcyclopropanecarbonyl chloride;A844779;racemic trans-2-phenyl-cyclopropane carbonyl chloride;Cyclopropanecarbonyl chloride, 2-phenyl-, trans- (8CI);trans-2-Phenyl-1-cyclopropanecarbonyl chloride, technical grade, 90%

Chemical Property of trans-2-Phenylcyclopropanecarbonyl chloride

Chemical Property:

• Vapor Pressure: 0.00438mmHg at 25°C
• Refractive Index: n20/D 1.556(lit.)
• Boiling Point: 278°Cat760mmHg
• Flash Point: 139.3°C
• PSA: 17.07000
• Density: 1.258g/cm³
• LogP: 2.55550
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 180.0341926
• Heavy Atom Count: 12
• Complexity: 184

Purity/Quality:

97% ^*data from raw suppliers

trans-2-Phenyl-1-cyclopropanecarbonyl chloride technical grade, 90% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1C(=O)Cl)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H]([C@@H]1C(=O)Cl)C2=CC=CC=C2
• Uses: trans-2-Phenyl-1-cyclopropanecarbonyl chloride was used in the synthesis of series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines.

Technology Process of trans-2-Phenylcyclopropanecarbonyl chloride

There total 8 articles about trans-2-Phenylcyclopropanecarbonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

trans-2-phenylcyclopropane-1-carboxylic acid (939-90-2) → (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride (939-87-7,5685-36-9,37107-48-5,42916-08-5,42916-12-1,42916-13-2,62624-90-2,78738-39-3)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; benzene; for 3h; Heating;

DOI:10.1021/ja00053a031

Reference yield:

(E)-3-phenylacrylic acid (140-10-3) → (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride (939-87-7,5685-36-9,37107-48-5,42916-08-5,42916-12-1,42916-13-2,62624-90-2,78738-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CuCr₂O₄; 1-butyl-3-methylimidazolium hydroxide / tetrahydrofuran / 4 h / 20 - 50 °C

2: chloroformic acid ethyl ester; triethylamine / toluene / 4 h / Cooling with ice

With 1-butyl-3-methylimidazolium hydroxide; CuCr₂O₄; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1007/s11164-016-2572-1

Reference yield:

2-phenyl-cyclopropanecarboxylic acid (5685-38-1) → 2-phenyl-1-cyclopropanecarbonyl chloride (939-87-7,5685-36-9,37107-48-5,42916-08-5,42916-12-1,42916-13-2,62624-90-2,78738-39-3)

Guidance literature:

With thionyl chloride;

DOI:10.1002/hlca.19860690720

upstream raw materials:

(1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid

trans-2-phenylcyclopropane-1-carboxylic acid

2-phenyl-cyclopropanecarboxylic acid

ethyl 2-phenylcyclopropylcarboxylate

Downstream raw materials:

C₂₃H₁₉ClN₂O₂

N-{4-[4-(2-phenylcyclopropanecarbonyl)piperazine-1-sulfonyl]phenyl}acrylamide

trans-N-(2-Hydroxy-aethyl)-2-phenyl-cyclopropancarbonsaeureamid