(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone

ChemicalBook > CAS DataBase List > (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone

Product Name: (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
CAS No.: 895152-66-6
Chemical Name: (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Synonyms: UR-144 Impurity 3;tert-butyl 4-acetoxy-octahydroindole-1-carboxylate;(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone;Methanone, 1H-indol-3-yl(2,2,3,3-tetramethylcyclopropyl)-
CBNumber: CB72490299
Molecular Formula: C16H19NO
Formula Weight: 241.33
MOL File: 895152-66-6.mol

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(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Property

Boiling point:: 375.0±15.0 °C(Predicted)
Density: 1.099±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMF: 50 mg/ml; DMF:PBS (pH 7.2); (1:7): 0.13 mg/ml; DMSO: 33 mg/ml; Ethanol: 17 mg/ml
form: A crystalline solid
pka: 15.50±0.30(Predicted)
InChI: InChI=1S/C16H19NO/c1-15(2)14(16(15,3)4)13(18)11-9-17-12-8-6-5-7-10(11)12/h5-9,14,17H,1-4H3
InChIKey: WYZQBEQQQKCTHM-UHFFFAOYSA-N
SMILES: C(C1C2=C(NC=1)C=CC=C2)(C1C(C)(C)C1(C)C)=O

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 9001966
Product name: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Purity: ≥98%
Packaging: 1mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 9001966
Product name: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Purity: ≥98%
Packaging: 5mg
Price: $356
Updated: 2024/03/01

Cayman Chemical

Product number: 9001966
Product name: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Purity: ≥98%
Packaging: 10mg
Price: $632
Updated: 2024/03/01

TRC

Product number: I655500
Product name: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Packaging: 1mg
Price: $65
Updated: 2021/12/16

TRC

Product number: I655500
Product name: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Packaging: 5mg
Price: $255
Updated: 2021/12/16

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(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Chemical Properties,Usage,Production

Description

UR-144 and XLR11 are potent synthetic cannabinoids (CBs) that have been identified as adulterants of herbal products. (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is the scaffold for UR-144, XLR11, and a number of additional synthetic CBs. The tetramethylcyclopropyl group typically confers selectivity for the peripheral CB₂ receptor. However, the addition of substituents at the N1-amine of the aminoalkylindole group is necessary for high affinity at either CB₁ or CB₂. This product is intended for forensic and research applications.

Uses

(1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is the scaffold for UR-144, XLR11, and a number of additional synthetic CBs. The tetramethylcyclopropyl group typically confers selectivity for the peripheral CB2 receptor

Definition

ChEBI: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is a member of indoles.

Synthesis

To a solution of indole (11 g, 95 mmol) in 30 mL of dichloromethane at ambient temperature was added 105 mL of a 1 M solution of ethyl magnesium bromide in tetrahydrofuran (THF) (105 mmol) δropwise via syringe pump. After the addition was complete, the solution was stirred for 15 min at which time 105 mL of a 1 M solution of ZnCl2 in Et2O (105 mmol) was added. The mixture was stirred for an additional 30 min, and then 2,2,3,3-tetramethylcyclopropane carbonyl chloride (95 mmol) in 50 mL of dichloromethane was added via cannula. The mixture was stirred for 6 h at ambient temperature and then was quenched with 50 mL of saturated, aqueous NH4Cl and diluted with 50 mL of dichloromethane. The layers were separated, and the aqueous layer was extracted with dichloromethane (3 × 30 mL). The combined organics were washed with 20 mL of H2O and then were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified via column chromatography (SiO2, 50% ethyl acetate/ hexanes) to give 9.7 g of the major regioisomer (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (40 mmol, 42% yield) and 6.1 g of the minor regioisomer of 1-[(2,2,3,3-tetramethylcyclopropyl) carbonyl]-1H-indole (25 mmol, 27% yield). 1H NMR (major product) (300 MHz, CD3OD) δ ppm 1.32 (s, 6 H), 1.33 (s, 6 H), 2.14 (s, 1 H), 7.12-7.24 (m, 2 H), 7.38-7.46 (m, 1 H), 8.02 (s, 1 H), 8.19-8.25 (m, 1 H); 1H NMR (minor product) (300 MHz, CD3OD) δ ppm 1.29 (s, 6 H), 1.34 (s, 6 H), 1.94 (s, 1 H), 6.66 (dd,J =3.7, 0.7 Hz, 1 H), 7.16-7.32 (m, 2 H), 7.51-7.58 (m, 1 H), 7.67 (d, J = 3.7 Hz, 1 H), 8.32-8.39 (m, 1 H); MS (major and minor regioisomers) (DCI/NH3) m/z 242 (M + H) + .

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone manufacturers

Dorne Chemical Technology co. LTD

Product: (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 895152-66-6
Price: US $10.00/ASSAYS
Min. Order: 1ASSAYS
Purity: 99%
Supply Ability: 100kg
Release date: 2024-03-26

Shandong Hanjiang Chemical Co., Ltd

Product: (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 895152-66-6
Price: US $0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10T
Release date: 2024-01-19

Hebei Anlijie Biotechnology Co., Ltd

Product: (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 895152-66-6
Price: US $3500.00-2800.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 500kg
Release date: 2023-12-21

895152-66-6, (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanoneRelated Search:

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone

tert-butyl 4-acetoxy-octahydroindole-1-carboxylate

Methanone, 1H-indol-3-yl(2,2,3,3-tetramethylcyclopropyl)-

UR-144 Impurity 3

895152-66-6