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Chemical Structure| 102-92-1 Chemical Structure| 102-92-1
Chemical Structure| 102-92-1

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Synonyms: Cinnamoyl chloride

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Product Details of Cinnamoyl chloride

CAS No. :102-92-1
Formula : C9H7ClO
M.W : 166.60
SMILES Code : O=C(Cl)C=CC1=CC=CC=C1
Synonyms :
Cinnamoyl chloride
MDL No. :MFCD00000732
InChI Key :WOGITNXCNOTRLK-VOTSOKGWSA-N
Pubchem ID :5354261

Safety of Cinnamoyl chloride

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Application In Synthesis of Cinnamoyl chloride

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 102-92-1 ]

[ 102-92-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 3469-20-3 ]
  • [ 102-92-1 ]
  • 1-<i>trans</i>-cinnamoyl-2,3-diphenyl-indole [ No CAS ]
  • 3
  • [ 2078-71-9 ]
  • [ 102-92-1 ]
  • <i>N</i>-(2-<i>trans</i>-cinnamoyloxy-ethyl)-<i>N</i>'-<i>trans</i>-cinnamoyl-urea [ No CAS ]
  • 5
  • [ 1197-10-0 ]
  • [ 102-92-1 ]
  • 6-carboxy-2-pyridylmethyl cinnamate [ No CAS ]
  • 6
  • [ 20469-61-8 ]
  • [ 102-92-1 ]
  • [ 113450-91-2 ]
  • 7
  • [ 56766-24-6 ]
  • [ 102-92-1 ]
  • [ 15298-36-9 ]
  • 8
  • [ 21617-20-9 ]
  • [ 102-92-1 ]
  • 6-Chloro-1-[(E)-(3-phenyl-acryloyl)]-2,3-dihydro-1H-quinolin-4-one [ No CAS ]
  • 9
  • [ 102-92-1 ]
  • (+-)-2-amino-1-<4-methoxy-phenyl>-ethanol [ No CAS ]
  • [ 15298-36-9 ]
  • 10
  • [ 2346-00-1 ]
  • [ 102-92-1 ]
  • (E)-1-(2-Methylene-thiazolidin-3-yl)-3-phenyl-propenone [ No CAS ]
  • 11
  • [ 92914-74-4 ]
  • [ 102-92-1 ]
  • (E)-3-cinnamoylaminoisoxazolo[5,4-b]pyridine [ No CAS ]
  • 12
  • [ 102-92-1 ]
  • [ 59804-37-4 ]
  • 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-thieno[2,3-e][1,2]thiazin-4-yl 3-phenylprop-2-enoate hydrochloride [ No CAS ]
  • 13
  • [ 102-92-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-glucopyranosyl-7-cinnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one [ No CAS ]
  • 14
  • [ 102-92-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one [ No CAS ]
  • 15
  • [ 102-92-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-tetracinnamoylglucopyranosyl-7-cynnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one [ No CAS ]
  • 16
  • [ 443-86-7 ]
  • [ 102-92-1 ]
  • [ 944407-13-0 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate; In water; ethyl acetate; at 0℃; Examples 12 and 13 2-({4-[(6,7-Dihydro[l,4]dioxino[2,3-c]pyridazin-3- yImethyI)amino]-l-piperidinyl}methyl)-9-fluoro-l,2-dihydro-4H-pyrrolo[3,2,l- i/]quinoIin-4-one hydrochloride, Enantiomers 1 and 2 <n="41"/>(a) (2SJS)- 1 , 1 -Dimethylethyl { 1 -[(9-fluoro-4-oxo- 1 ,2-dihydro-4H-pyrrolo[3,2, 1 - ij]quinolin-2-yl)methyl]-4-piperidinyl}carbamateMethod A(1) (2E)-N-(3-Fluoro-2-methylphenyl)-3-phenyl-2-propenamide; A solution of cinnamyl chloride (100 g, 610 mmol) in ethyl acetate (400 ml) was added to a vigorously-stirred mixture of <strong>[443-86-7]3-fluoro-2-methylaniline</strong> (75 g, 400 mmol), saturated aqueous sodium bicarbonate (850 ml), ice (ca 100 g) and ethyl acetate (400 ml). After 1 hour the mixture was concentrated on a rotary evaporator (removing most of the ethyl acetate) and filtered, washing with water. The resulting white solid was dried in vacuo (-160 g, 100percent).MS (+ve ion electrospray) m/z 256 (MH+).
100% With sodium hydrogencarbonate; In water; ethyl acetate; for 0.283333h; (a) (2E)-N-(3-Fluoro-2-methylphenyl)-3-phenyl-2-propenamideA solution of cinnamyl chloride (100 g, 610 mmol) in ethyl acetate (400 ml) was added to a vigorously-stirred mixture of <strong>[443-86-7]3-fluoro-2-methylaniline</strong> (75 g, 600 mmol), saturated aqueous sodium bicarbonate (850 ml), ice (ca 100 g) and ethyl acetate (400 ml) over 2 min. After 0.25 hour the mixture was filtered, washing with water, more solids coming out of the filtrate and so refiltered. The resulting solid was dried in vacuo (160 g, 100percent).MS (+ve ion electrospray) m/z 256 (MH+).
  • 17
  • [ 7499-66-3 ]
  • [ 102-92-1 ]
  • 6-bromo-β-naphthylcinnamide [ No CAS ]
  • 18
  • [ 443-86-7 ]
  • [ 102-92-1 ]
  • [ 944407-13-0 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate; In water; ethyl acetate; at 0℃; for 0.25h; A solution of cinnamyl chloride (100 g, 610 mmol) in ethyl acetate (400 ml) was added to a vigorously-stirred mixture of <strong>[443-86-7]3-fluoro-2-methylaniline</strong> (75 g, 600 mmol), saturated aqueous sodium bicarbonate (850 ml), ice (ca 100 g) and ethyl acetate (400 ml) over 2 min. After 0.25 hour the mixture was filtered, washing with water, more solids coming out of the filtrate and so refltered. The resulting solid was dried in vacuo (-160 g, 100percent). MS (+ve ion electrospray) m/z 256 (MH+).
  • 19
  • [ 6645-46-1 ]
  • [ 102-92-1 ]
  • [ 1044499-00-4 ]
  • 20
  • [ 367-34-0 ]
  • [ 102-92-1 ]
  • 2,4,5-trifluoroanilide of cinnamic acid [ No CAS ]
  • 21
  • [ 102-92-1 ]
  • [ 7149-75-9 ]
  • [ 1161429-02-2 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; In dichloromethane; at 0 - 20℃; for 2h; To <strong>[7149-75-9]4-chloro-3-methylaniline</strong> (3.33 g, 19.98 mmole) in dichloromethane (100 mL) and pyridine (20 mL) was added cinnamoyl chloride (2.83 g, 19.98 mmole) at 00C. The mixture was stirred at room temperature for 2 h. Solvent and pyridine were removed by rotary evaporator under reduced pressure. The residue was diluted with ethyl acetate and washed IN HCl (2 x 100 mL), water (2 x 100 mL), sodium bicarbonate solution (2 x 10OmL) and dried over sodium sulfate. After removing solvent a white solid was recovered (5.38 g, 99percent yield). The product was used for the next step without further purification. 1H NMR (400 MHz, DMSOd6): delta 7.76-7.24 (m, 10H), 6.58(d, IH), 2.55 (s, 3H); MS (ESI) m/z: Calculated for C16H14ClNO: 271.1; found: 272 (M+H)+.
99% With pyridine; In dichloromethane; at 20℃; for 2h; N-(4-Chloro-3-methylphenyl)cinnamamide To <strong>[7149-75-9]4-chloro-3-methylaniline</strong> (3.33 g, 19.98 mmole) in dichloromethane (100 mL) and pyridine (20 mL) was added cinnamoyl chloride (2.83 g, 19.98 mmole) at 0° C. The mixture was stirred at room temperature for 2 h. Solvent and pyridine were removed by rotary evaporator under reduced pressure. The residue was diluted with ethyl acetate and washed 1N HCl (2*100 mL), water (2*100 mL), sodium bicarbonate solution (2*100 mL) and dried over sodium sulfate. After removing solvent a white solid was recovered (5.38 g, 99percent yield). The product was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6): delta 7.76-7.24 (m, 10H), 6.58 (d, 1H), 2.55 (s, 3H); MS (ESI) m/z: Calculated for C16H14ClNO: 271.1. found: 272 (M+H)+.
  • 22
  • [ 10234-66-9 ]
  • [ 102-92-1 ]
  • (E)-1-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-3-phenylprop-2-ene-1-one [ No CAS ]
  • 23
  • [ 24630-67-9 ]
  • [ 102-92-1 ]
  • [ 1352612-17-9 ]
  • 24
  • [ 102-92-1 ]
  • [ 22259-53-6 ]
  • C18H16N2O [ No CAS ]
  • 25
  • [ 5417-17-4 ]
  • [ 102-92-1 ]
  • S-(6-formyl-2,3-dimethoxyphenyl) (E)-3-phenylprop-2-enethioate [ No CAS ]
  • 26
  • [ 443-86-7 ]
  • [ 102-92-1 ]
  • [ 944407-14-1 ]
  • 27
  • [ 443-86-7 ]
  • [ 102-92-1 ]
  • N-(3-fluoro-2-methylphenyl)cinnamamide [ No CAS ]
  • 28
  • [ 102-92-1 ]
  • [ 480-39-7 ]
  • 29
  • [ 102-92-1 ]
  • [ 436-77-1 ]
  • 7-O-(3-phenyl-2-acryloyl)-fangchinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: Acyl chloride (0.18 mmol, 1.1 eq) was added at 0 C to a solution of <strong>[436-77-1]fangchinoline</strong> (100 mg, 0.16 mmol) and DMAP (0.032 mmol, 0.2eq) in 2 mL dry CH2Cl2 under argon and stirred for 2-4 h. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted three times with CH2Cl2. The combined organic phase was dried over anhydrous magnesium sulfate before vacuum suction filtration. The removal of the solventin vacuo afforded the crude product, which was chromatographied on silica gel (CH2Cl2/MeOH, 50/1 v/v, 0.1% TEA) to provide the pureproduct 1a-1e, 2a-2g, 3a-3e and 4a-4h.
67% General procedure: Fangchinoline (100 mg, 0.16 mmol) was dissolved in 8 mL of CH2Cl2. The mixture was cooled to 0 C under N2. Pyridine (25 mg, 0.32 mmol) was added to the mixture. The solution was stirred for 1 h and various types of acyl chlorides (0.24 mmol, in 2 mL of CH2Cl2) were added dropwise over 10 min. The mixture was stirred for 1 h at 0 C and was stirred another hour at room temperature. The mixture was washed with water, dried over anhydrous Na2SO4 and filtered. After being concentrated under vacuum, the residue was purified by flash chromatography on silica gel using CH2Cl2/CH3OH as eluant to afford the desired products 6a-6p.
  • 30
  • [ 367-34-0 ]
  • [ 102-92-1 ]
  • C15H10F3NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; acetone; at 0 - 20℃; for 3h; General procedure: To a mixture of fluoroaniline and K2CO3 in acetone-water cooled in an ice bath, cinnamoyl chloride was added in small portions.The mixture was stirred at 0°C for 2 h and held at 20°C for 1 h. The precipitated material was filtered off, washed with water and dried.
  • 31
  • [ 61019-05-4 ]
  • [ 102-92-1 ]
  • C19H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; at 20℃; for 1.0h; To a 250 ml round bottom flask was added 7-methyl-5-methoxy-lH-indole (50 mmol)Add 100 ml of toluene to mix it,Further addition of cinnamoyl chloride (60 mmol)Room temperature reaction for 1 hour,After the compound has been completely precipitated,Phenylhydrazine (60 mmol) was added,Heated to 105 C with a heating jacket,Placed on a magnetic stirrer,The reaction was heated under reflux for 6 hours,Reaction process constantly point observation,After the reaction is complete, the heating is stopped and the condensing unit is removed.The reaction solution was distilled and concentrated, and the product was isolated by column chromatography.The crude product was recrystallized from an ethanol-water solution, dried,The product was obtained (pale pink solid 12.71 g, yield 80.2%).
  • 32
  • [ 27757-86-4 ]
  • [ 102-92-1 ]
  • N-(thiophen-3-ylmethyl)cinnamamide [ No CAS ]
  • 33
  • [ 102-92-1 ]
  • [ 2986-17-6 ]
  • N-cinnamoyl-N,N′-diisopropylthiourea [ No CAS ]
  • 34
  • [ 102-92-1 ]
  • [ 494-52-0 ]
  • N-cinnamoylanabasine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In benzene; at 20℃; for 3.0h; 1.81 g (0.018 mol) of triethylamine and a solution of 3.0 g (0.018 mol) of cinnamoyl chloride in 50 mL of benzene were added at stirring to a solution of 3 g (0.018 mol) of anabasine in 150 mL of benzene. The reaction mixture was stirred during 3 h at room temperature until the precipitate formation. Precipitate of triethylammonium chloride was filtered off, the filtrate was evaporated, and the residue was purified by chromatography on alumina (eluents: benzene or 100 : 1 benzene-ethyl acetate). Yield 3.9 g (75%), white crystals, mp 96-98C. 1H NMR spectrum, delta, ppm (J, Hz): 1.30-1.42 m (1H, H11ax), 1.54-1.57 (2H, H11eq,10ax), 1.79 br. s (1H, H10eq), 2.36-2.46 m (1H, H12ax), 2.87 br. s (1H, H12eq), 3.43-3.46 m (1H, H9ax), 4.22 br. s (1H, H9eq), 5.87 br. s (1H, H7), 7.30-7.34 m (5H, H5,18,19,21,22), 7.56-7.69 m (4H, H4,15,16,20), 8.4-8.47m (2H, H2,6). 13C NMR spectrum, deltaC, ppm: 19.72 (C11), 26.19 (C10), 27.61 (C12), 48.23 (C9), 49.84 (C7), 118.83 (C15), 124.13 (C5), 128.58 (C3), 128.80 (C20), 129.23 (C19,23), 130.05 (C18,22), 134.92 (C4), 135.68 (C17), 142.68 (C16), 148.28 (C6), 148.65 (C2), 166.7 (C13).
  • 35
  • [ 138326-68-8 ]
  • [ 102-92-1 ]
  • C15H17NO3 [ No CAS ]
 

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