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
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
Shaanxi Dideu Medichem Co. Ltd
Product
(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 895152-66-6
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1000KG
Release date
2024-08-13

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
  • 895152-66-6