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Chemical Structure| 16420-13-6 Chemical Structure| 16420-13-6

Structure of Dimethylthiocarbamoyl chloride
CAS No.: 16420-13-6

Chemical Structure| 16420-13-6

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Product Details of [ 16420-13-6 ]

CAS No. :16420-13-6
Formula : C3H6ClNS
M.W : 123.60
SMILES Code : ClC(N(C)C)=S
MDL No. :MFCD00004919
InChI Key :PHWISQNXPLXQRU-UHFFFAOYSA-N
Pubchem ID :27871

Safety of [ 16420-13-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H317
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 16420-13-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 0
Fraction Csp3 0.67
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 32.02
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

35.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.82
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.38
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.07
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.6
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.33
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.24

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.41
Solubility 4.81 mg/ml ; 0.0389 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.73
Solubility 2.33 mg/ml ; 0.0188 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.71
Solubility 23.9 mg/ml ; 0.193 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.07 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.79

Application In Synthesis of [ 16420-13-6 ]

* 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 [ 16420-13-6 ]

[ 16420-13-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 605-32-3 ]
  • [ 16420-13-6 ]
  • [ 2951-23-7 ]
  • 2
  • [ 6812-16-4 ]
  • [ 16420-13-6 ]
  • [ 88791-22-4 ]
  • 3
  • [ 5985-24-0 ]
  • [ 16420-13-6 ]
  • [ 1026002-47-0 ]
  • 4
  • [ 39224-65-2 ]
  • [ 16420-13-6 ]
  • dimethyl-thiocarbamic acid <i>O</i>-(4,5-dichloro-2-nitro-phenyl) ester [ No CAS ]
  • 5
  • [ 10323-39-4 ]
  • [ 16420-13-6 ]
  • [ 1219832-24-2 ]
YieldReaction ConditionsOperation in experiment
Example 22N-{4-[7-tert-Butyl-5-(2-oxo-1,2-dihydro-pyridin-3-yl)-benzo[b]thiophene-3-carbonyl]-morpholin-2-ylmethyl}-methanesulfonamide (112) step 1 -The neat thiocarbamate 102a (9.2 g, prepared by acylation of 2-tert-butyl-4-bromo-phenol with N,N-dimethyl thiocarbamoyl chloride) was heated with a heat gun for 20 min. (At 20 min extraneous peaks began to be detectable by TLC). The reactant was cooled and purified by SiO2 chromatography (Analogix, 80 g) eluting with an EtOAc/hexane gradient to afford 4.6 g (50%) of 102b as a light brown solid.
  • 6
  • [ 22717-55-1 ]
  • [ 16420-13-6 ]
  • [ 115768-61-1 ]
YieldReaction ConditionsOperation in experiment
With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; for 20h; b) 4-Chloro-2-dimethylthiocarbamoyloxy-benzoic acid methyl ester [0331] To a mixture of the above ester (6.48 g, 34.7 mmol) in DMF (40 mL) was added DABCO (11.6 g, 104 mmol) and dimethylthiocarbamoyl chloride (4.5 g, 36.5 mmol). The resultant mixture was stirred at rt for 20 h and poured into EtOAc / I N HCl aq solution. Organic phase was washed with 1 N HCl solution, saturated NaHCO3 solution and brine. It was filtered, dried over Na2SO4, filtered and concentrated to provide the title compound (8.86 g) as pale yellow solid. 1H NMR (200 MHz, CDCl3): delta (ppm) = 7.93 (d, J = 8.2 Hz, 1 H), 7.28 (dd, J = 8.5, 2.2 Hz, 1 H), 7.13 (d, J = 2.0 Hz, 1 H). 3.83 (s, 3 H), 3.46 (s, 3 H), 3.38 (s, 3 H).
  • 7
  • [ 1139-52-2 ]
  • [ 16420-13-6 ]
  • [ 2455-14-3 ]
  • [ 128-38-1 ]
  • [ 1569938-94-8 ]
  • 8
  • [ 16420-13-6 ]
  • [ 939-69-5 ]
  • O-(2-cyanobenzo[d]thiazol-6-yl)dimethylcarbamothioate [ No CAS ]
  • 9
  • [ 95-54-5 ]
  • [ 16420-13-6 ]
  • [ 2851-13-0 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; copper(l) iodide; sodium hydroxide; at 60℃; for 0.166667h;Microwave irradiation; Green chemistry; Add 1 mmol of o-phenylenediamine to the reaction vessel.Add 0.05 mmol of cuprous iodide sequentially.1 mmol of sodium hydroxide, N,N-dimethylaminothioformyl chloride 2.5 mmol,3 ml pyridine.Heated to 60 C at 120 W in a microwave reactorContinuous reaction for 10 min.After the reaction is completed, it is cooled to room temperature.Concentrated under reduced pressure,The product is purified by column chromatography.A white solid was obtained in 88% yield.
87% With iron(III) chloride; caesium carbonate; In tetrahydrofuran; at 60℃; for 5.0h;Green chemistry; Add 1 mmol of o-phenylenediamine to the reaction vessel.Add 0.1 mmol of ferric chloride in sequence,Cesium carbonate 1 mmol,N,N-dimethylaminothioformyl chloride 2.5 mmol,3 ml of tetrahydrofuran. Heat to 60 C for 5 h. After the reaction is completed, it is cooled to room temperature.Concentrated under reduced pressure, the product was purified by column chromatography.A white solid was obtained in a yield of 87%.
  • 10
  • [ 72955-97-6 ]
  • [ 16420-13-6 ]
  • O-(5-fluoro-2-methoxyphenyl)-N,N-dimethylthiocarbamate [ No CAS ]
  • 11
  • [ 5369-19-7 ]
  • [ 16420-13-6 ]
  • [ 611226-35-8 ]
YieldReaction ConditionsOperation in experiment
In toluene; for 5h;Reflux; General procedure: Taking the synthesis of 18 3-(trifluoromethyl)phenyl 1-isothiocyanate as an example, 19 3-(trifluoromethyl)aniline (2.38g, 14.77mmol, 1 eqv) and 20 dimethylamino thiocarbonyl chloride (1.92g, 15.50mmol, 1.05 eqv) were added in dry 21 toluene (20mL) at room temperature, and then the reaction mixture was refluxed for 5h. After the reaction mixture was cooled down to room temperature, the solid dimethylamine hydrochloride was filtered off, and the collected toluene fraction was removed under reduced pressure. Colorless oil (2.55g, 85%) was obtained and used in the next step without additional purification. The other aromatic isothiocyanates were synthesized in the same way.
 

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